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343641

Sigma-Aldrich

(R)-(+)-Citronellal

technical grade

Synonym(s):

(+)-Citronellal, (3R)-3,7-Dimethyl-6-octenal

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2CH(CH3)CH2CHO
CAS Number:
2385-77-5
Molecular Weight:
154.25
Beilstein:
1720791
EC Number:
219-194-5
MDL number:
MFCD00067089
UNSPSC Code:
12352114
PubChem Substance ID:
24861185
NACRES:
NA.22
Pricing and availability is not currently available.

grade

technical grade

form

liquid

refractive index

n20/D 1.448 (lit.)

bp

207 °C (lit.)

density

0.851 g/mL at 25 °C (lit.)

functional group

aldehyde

SMILES string

C[C@H](CC\C=C(\C)C)CC=O

InChI

1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3/t10-/m1/s1

InChI key

NEHNMFOYXAPHSD-SNVBAGLBSA-N

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General description

(R)-(+)-Citronellal is a monoterpenoid aldehyde. It is a chiral organic compound used as a building block in organic synthesis to prepare various chiral compounds. It is also used as a chiral catalyst or ligand in asymmetric reactions.

Application

(R)-(+)-Citronellal can be used as a reactant to synthesize various compounds such as L-menthol, caparratriene, and chalcogen-containing nitrone derivatives.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

167.0 °F - closed cup

Flash Point(C)

75 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCG7493
MKBZ8929V
MKBV6412V
MKBM0881V
08214PR

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Xiangxian Ying et al.
Molecules (Basel, Switzerland), 24(6) (2019-03-21)
The members of the Old Yellow Enzyme (OYE) family are capable of catalyzing the asymmetric reduction of (E/Z)-citral to (R)-citronellal-a key intermediate in the synthesis of L-menthol. The applications of OYE-mediated biotransformation are usually hampered by its insufficient enantioselectivity and
Walter S Leal et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(46), 18704-18709 (2013-10-30)
The southern house mosquito, Culex quinquefasciatus, has one of the most acute and eclectic olfactory systems of all mosquito species hitherto studied. Here, we used Illumina sequencing to identify olfactory genes expressed predominantly in antenna, mosquito's main olfactory organ. Less
Gabriele Siedenburg et al.
Applied and environmental microbiology, 78(4), 1055-1062 (2011-12-14)
The biosynthesis of cyclic monoterpenes (C(10)) generally requires the cyclization of an activated linear precursor (geranyldiphosphate) by specific terpene cyclases. Cyclic triterpenes (C(30)), on the other hand, originate from the linear precursor squalene by the action of squalene-hopene cyclases (SHCs)
Alina Mariana Balu et al.
Organic & biomolecular chemistry, 8(12), 2845-2849 (2010-05-01)
The selective conversion of citronellal to menthols, with good diastereoselectivities to (-)-menthol for the case of (+)-citronellal as starting material, can effectively be carried out in a one-step reaction under microwave irradiation catalysed by supported nanoparticles on mesoporous materials. 2%
Marisa Belicchi-Ferrari et al.
Journal of inorganic biochemistry, 104(2), 199-206 (2009-12-08)
This paper reports the syntheses and characterization of ethylmorpholine substituted citronellal thiosemicarbazone copper(II) and nickel(II) metal complexes. The compounds were characterized through elemental analyses and spectroscopic (IR, UV-Vis, NMR, MS) methods. The X-ray analysis of the two complexes shows that
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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